Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2007(7): 1033-1037
DOI: 10.1055/s-2007-965960
DOI: 10.1055/s-2007-965960
PAPER
© Georg Thieme Verlag Stuttgart · New York
Total Synthesis of Vulnibactin: A Natural Product Iron Chelator
Further Information
Received
15 November 2006
Publication Date:
28 February 2007 (online)
Publication History
Publication Date:
28 February 2007 (online)

Abstract
A short, high-yield, flexible synthesis is described for accessing vulnibactin and related siderophores, e.g., vibriobactin analogues and homologues. The spectral properties of the synthetic vulnibactin are identical with those reported for the natural product, thus confirming the proposed structure of vulnibactin.
Key words
chelates - iron - medicinal chemistry - natural products - receptors
- 1
Raymond KN.Carrano CJ. Acc. Chem. Res. 1979, 12: 183 -
2a
Winkelmann G. Biochem. Soc. Trans. 2002, 30: 691 -
2b
Albrecht-Gary AM.Crumbliss AL. In Metal Ions in Biological Systems Vol. 35:Sigel A.Sigel H.Sigel K. Taylor & Francis; New York: 1998. p.239 -
2c
Neilands JB. Annu. Rev. Biochem. 1981, 50: 715 - 3
Tait GH. Biochem. J. 1975, 146: 191 - 4
Bergeron RJ.Xin MG.Weimar WR.Smith RE.Wiegand J. J. Med. Chem. 2001, 44: 2469 - 5
Bergeron RJ.Garlich JR.McManis JS. Tetrahedron 1985, 41: 507 - 6
Okujo N.Saito M.Yamamoto S.Yoshida T.Miyoshi S.Shinoda S. BioMetals 1994, 7: 109 -
7a
Peterson T.Neilands JB. Tetrahedron Lett. 1979, 20: 4805 -
7b
Peterson T.Falk K.-E.Leong SA.Klein MP.Neilands JB. J. Am. Chem. Soc. 1980, 102: 7715 - 8
Choi M.-H.Sun H.-Y.Park R.-Y.Kim C.-M.Bai Y.-H.Kim Y.-R.Rhee J.-H.Shin S.-H. FEMS Microbiol. Lett. 2006, 257: 285 - 9
Diarra MS.Lavoie MC.Jacques M.Darwish I.Dolence EK.Dolence JA.Ghosh A.Ghosh M.Miller MJ.Malouin F. Antimicrob. Agents Chemother. 1996, 40: 2610 - 10
Krapcho AP.Kuell CS. Synth. Commun. 1990, 20: 2559 - 11
Loughlin WA.Knevitt SA.Hosking RE.Marshall RL. Aust. J. Chem. 2000, 53: 457 - 12
Bergeron RJ.Kline SJ. J. Am. Chem. Soc. 1984, 106: 3089